


Room Service

by ATOTENSHI



Category: Mafia (Video Games)
Genre: Crossdressing Kink, Implied/Referenced Cheating, Light BDSM, M/M, Master/Slave, Situational Humiliation, Verbal Humiliation
Language: English
Status: Completed
Published: 2021-02-21
Updated: 2021-02-21
Packaged: 2021-03-18 01:55:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,850
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29602083
Author URL: https://archiveofourown.org/users/ATOTENSHI/pseuds/ATOTENSHI
Summary: Room service is common in hotels and homes alike, but Henry is looking for a different kind of service.....
Relationships: Vito Scaletta/Henry Tomasino
Comments: 1
Kudos: 8





	Room Service

**Author's Note:**

  * For [justreallybored](https://archiveofourown.org/users/justreallybored/gifts).



> Songs/playlist : Do You Feel This Way--Kailee Morgue, Gangsta--Trixidy, Aphrodite--RINI, Authority--Of Methodist, Own2--April+VISTA, Spell--NIKI, After Dark--Mr. Kitty, Heavy--POWERS, Poison--Girl Friend, Lips of an Angel--Hinder, Smoke--Bobi Andonov 

Vito loved it. He loved every last inch of it. He stood in the mirror, checking himself out, twirling and pruning. He thought he looked right pretty in his ebony maid outfit, bubblegum lace and thigh highs--black chunky heels to finish off the coordinate. He sat on blood-red blankets, his body sinking into the mattress--the outfit’s ruffles sailing on the satin surface. He took another look in the reflective glass as he sat so daintily, hands between his thighs, hidden by the ocean of black--his muscular, fuzzy legs hanging off the edge of the bed, swinging about. 

He took a deep breath and lay on the satin sheets, pulling away from his reflection--letting his mind wander to suggestive thoughts about what his dominant would do to him in that lecherous outfit. Perhaps a bit of edging with ice? No,...maybe the maid would be tied up and left there high and dry--forced to get himself off or wait for their boss to let them out of the bonds. His hand wandered to his chest as he imagined someone--that special someone--teasing his inner thighs and whispering lowly in his ear about what demeaning things they were going to do to him and his psyche. 

He exhaled shakily as he thought, “Man, I can’t believe I’m into this…” before feeling himself up again, bending his legs and spreading them. However, he was interrupted by a knock on the door. Vito quickly sat up, smoothing out his dress.

“Yeah, ah..who--who is it?” he asked with a slight crack in his voice.

The door creaked open, revealing his master's handsome visage. “Did I interrupt something, Vito?” he asked.

Vito cleared his throat and shook his head slightly.

“No." he said hurriedly.

Henry nodded and continued to speak. “In that case, get off your ass." He claimed, " I need to see you in my office.”

*******************************************************************

Henry sat in his dimly-lit, mahogany office--a singular lamp illuminating a small amount of space around him. He had his legs crossed on his shiny, oak, desk-- a book, open in his grasp. The bookshelf to his right needed some dusting and polishing, while some dishes needed to be carried to the kitchen for washing--something Henry's favorite housemaid could do at the snap of his calloused fingers.

Reading the prose presented before him, Henry waited with the utmost patience for his handsome servant to arrive; the thought of him embarrassed in a maid outfit forced a small smile onto his rugged face. 

“With fruit the vines that round the thatch-eaves run;

To bend with apples the moss'd cottage-trees,

And fill all fruit with ripeness to the core;

To swell the gourd, and plump the hazel shells

With a sweet kernel; to set budding more,---”

The door opened with a creek before Henry could finish reading, his manservant standing before him a couple of feet away from the desk.

“It's about damn time you got in here, Vito.” Henry said as he continued to read, not even lifting an eye off the page.

Vito bowed slightly, opening his painted, ruby lips to speak. 

“Is there something you wanted from me, Henry?” he spoke softly.

Henry hummed as he put the book down.

“Yeah...” he replied before picking up a nearby pen and scribbling something on a stack of notes.

“But, I think we’ve forgotten a few rules since our last meeting, yeah?"

Vito stood up straight, hands clasped together, his fingers fidgeting about. 

“Address me as either 'Mister Tomasino' or sir.’” the man ordered, looking up at his young servant with cold eyes--forcing a shiver of arousal down Vito's spine.

“Ye-yes, sir…” he said as he got closer to the desk. 

There was Vito Scaletta, a man who didn’t take anything from anyone--yet here he was, taking every order from a man twice his age. Henry smirked as he watched a blush creep onto his olive skin. 

He sighed and looked up at him. “The bookshelf needs dusting and polishing, and the dishes need washing..” Henry told him, pointing to the respective items with a pen. 

Vito's eyes followed the writing utensil and nodded. “Yes, sir...in that order?”

Henry shrugged as he picked up the poetry book again. “The order doesn’t matter.,” he responded, turning back to the page he left off on.

Vito nodded and got to work on the wooden bookshelf almost immediately, grabbing the duster from the drawer near the shelf and removing books from their resting place. One book was stacked onto another, and another, and another, and another, until the pile of books had gotten too heavy to carry in the servant’s hand. Eventually, with a small 'oh shit!', the books toppled to the ground, one--maybe two at a time, the noise startling him and the Mister. He quickly scrambled to his stocking-clad knees and picked them up carefully. 

Henry shook his head and pushed his chair out, lifting up off the comfy cushion. He started towards him, the click-clack of his expensive shoes echoing on the wooden floor. Vito fell in love with the sound, mind going hazy as he anticipated his master's arrival.

“Goddammit, ” Henry cursed. “there’s nothing more useless than a clumsy maid!"

Vito felt his face warm up, boiling hot as if it were near a furnace.

“Can’t you do anything right?” he belittled some more. 

Vito stood up slowly, his face about as red as a poppy flower. 

“I-I’m sorry, Mr. Tomasino…” he apologized, avoiding the other’s piercing gaze.

Henry hummed and circled Vito slowly.

“A sorry excuse for a maid is what you are.” he crooned behind him.

Henry realized that the dress wasn’t as puffy as he willed it to be. How pitiful, the domestic servant couldn't even dress appropriately in the face of their employer.

“Say, Vito..” he started. “Do you got a petticoat under that dress of yours?” he asked suspiciously, eyeing his ruffles. “Bloomers?”

Vito fumbled his words and looked up at the tall, dark and handsome man, embarrassed about everything.

“Well, do ya?” The man inquired again.

Vito kept quiet as he looked away.

Having had enough of the mafioso-turned-maid’s mute games, Henry's face melted into a sneer. He stood back and disciplinary, strong arms folding themselves comfortably across his chest. 

“Lift up the skirt,” he ordered, a hiss lingering on his lips.

He looked shocked that Henry would demand such a thing, deep blue eyes wide with surprise.

“Don’t just look at me, lift it up!” he barked, growing impatient. “Or did you suddenly go deaf, you stupid housekeep?”

Henry's degrading forced Vito to shudder as he gripped the hem of his dark skirt, hesitating to lift it.

“Lift it. I'm not gonna say it again.” he threatened, stepping closer.

Vito lifted the garment slowly, looking down over his shoulder, his face still blotchy. 

Henry frowned with disappointment. Just as he thought--there wasn't a petticoat or bloomers under his costume, just bubblegum-lavender panties against flushed flesh--his manhood lying against his thigh, chubby, but not fully aroused. 

That frown flipped into a smirk at the revelation, studying the pretty intimates he had on.

“Well, lookie here~!” he whistled mockingly. “Did you go snooping around the lingerie section for these, you fuckin' pervert?” 

Vito lowered his arms in embarrassment at his master's jive, his eyebrows knitted in possible shame.

“Hey!” he called sharply, his jeering voice replaced by an annoyed one. “I didn’t tell you to put it down!" He said, giving Vito an icy glare.

He lifted it up again quickly, face significantly more carmine than it was before.

Henry hummed in approval, a small smile crawling onto his features. He walked up to the point of his nose, confident and cocky. “You’re such a little deviant, aren’t you?” he asked sweetly with a giggle.

Henry palmed his chubby, erection through the lightweight underwear. He enjoyed watching Vito shudder and sigh at the gentle touch, his eyes closed as Henry continued to humiliate him. He let out a chuckle and leaned into his ear, asking, “What d'ya think Joe would say if he found out that you're a stupid, fuckin' crosdresser, huh?” as his palming got a little rougher.

Vito chuckled before replying, “He'd make fun of me…” 

A satisfied hum escaped Henry's throat as he leaned away from his ear. He took another glance at Vito's lacy panties, noticing how hard he was in this moment. He hooked a finger under the waistband, pulling them down slightly before teasing him, rubbing a soft finger up and down the slit--causing the man to whimper.

"Please, sir...” he beseeched “c'mon, don’t tease me..”

Henry clicked his tongue and rolled his eyes as he pulled back the waistband on Vito's panties, listening with sadistic glee as the man let out a small yelp when the elastic snapped back on his dick. 

“I do what I want, sissy.” replied Henry harshly.

Vito winced a little before nodding--his eyes half-open.

“Of course, Mr. Tomasino.” he responded. “Uhm...but, may I put my arms down now?”

Henry took some steps back before looking him up and down as Vito stood there in such a degrading position. He moved his eyes towards Vito's wanton blue ones. With a small hum, he nodded head in compliance. “Yeah, go ahead” he assured.

The Italian man did as he was allowed and smoothed out his dress once again. Following his gaze, Henry watched him, intrigued to say the least. He couldn’t believe that someone like Vito would ever get off to this sort of thing, he wouldn’t have thought so in a million years. 

He realized how cute Vito looked in this getup, not to mention the deep red lipstick that he chose for himself. Henry could tell that his maid took his sweet time to get all dolled up for his pleasure. From the neatly pressed dress to his sheer stockings--it was indeed flattering. 

Henry's gaze drifted back to Vito's face--the rosy lipstick catching his eye again. He decided to comment on it.

“Look at you, getting all pretty for me, you think that’s cute?” Henry teased. “Wearing women's makeup on your lips?”

All Vito did was scoff and blush as Henry sauntered closer to him. Without so much as a warning, the older man shot an arm towards his servant’s chiseled face, his hand squeezing it tightly--the maid's lips squishing to form a puckered diamond shape.

“You think it’s cute?” he reiterated.

Vito quickly nodded his head, forcing his mouth into a tight line, tears of pleasure, rather, embarrassment pricking the corners of his eyes. Henry gradually loosened his grip on Vito's face, slowly dragging his calloused fingers down his features until they dripped off his square jaw. 

“Well, you look good enough to eat.” he complimented dryly--no positive emotion on his tongue. 

“Ah...thank you, sir,” he said with a faint smile, his tears rolling down tan cheeks.

Henry reached under his raunchy costume, pawing and feeling around for stiff, heated flesh. Once he found what he was looking for, he stroked him gently, feeling how Vito relaxed into his touch and sighed.

“You're fuckin' pathetic.” he began. “I've done nothing but emasculate you, and you’re as hard as a damn rock!"

Vito only chuckled at the comment, humiliated. The shame only fueled his rancid thoughts, the touch he was receiving only pushing him into a submissive state of mind.

“You like this shit, pretty boy? ” Henry questioned, eyebrows furrowed in feigned disgust. 

Vito let a shaky sigh escape his pretty, little, lips before answering with, “Yes sir, I--I do.”.

With this answer, Henry snickered, giving the man’s hard-on a tight squeeze--forcing his breath to hitch and liquid to leak.

“Jeez, you're sick.” he said, "Needy little bastard, aren’t ya?"

He nodded with a whine, his dick twitching longingly.

All Henry could do was look Vito in the eye as he relentlessly teased him. The young man was lucky he was cute. Vito looked up at Henry as if he were an angel, eyes pleading for his master's commands and control. Henry knew he wanted him to loot his body, to make him a servant to his sensuality--but he wasn't going to give poor Vito that prize. 

The maroon walls dripped with desire and want as Henry's strokes grew longer and slower, the walnut dresser and espresso bookshelf were still and noiseless--as if they were watching the spectacle in front of them. He found himself giving in to the servant’s desires, the thrust of Vito's hips and whimpers from his lips further proving this statement. A part of Henry wanted to give him what he longed for, but the other half wanted to take it away. 

“Look at you,” he began, tone as harsh as a hurricane wind, yet leaking with fervor, “whimpering n' shit when all I've done is touch you.”

Vito's mouth opened slightly, “I’m sorry, mister--”

“You’re always fuckin' sorry.” Henry stated, “Competent maids own up to their actions…”

Vito clammed up, then.

Henry removed his hand from the other’s loins and leaned forward, mouth up against his ear.

“Mmm? What happened, sissy?” he cooed, “you were whining' up a storm earlier!” 

With a prideful smirk, he put his hand back under the skirt--fondling tender skin and heavy jewels.

Carrying a furrowed brow and a flushed face, Vito let a groan fly from his mouth, saying, “Please, sir, I just want--”

Henry cocked an eyebrow. “Hm? What is it, Vito?” he interrupted, leaning away from his ear--his free hand hand cupping his chin--thumb drawing little circles on the broadest part.

The man stood back as he watched more tears prick at Vito's eyes, only to hastily cascade down his cheeks. Henry smiled, knowing how much Vito loved it, how much he adored Henry's bitter, backhanded compliments and teasing tone, how much he loved feeling inferior, how he took delight in letting his control slip into trusted hands, for those same hands to discipline and degrade him.

“...A kiss..please, sir.” he pleaded, softer than he had ever been that evening.

Vito wiped his face, clearing his throat, painted lips repeating that last word.

“Please, Mister Tomasino?”

Henry's passionate, gray eyes locked onto Vito's blessed ones as he stepped forward, a tender palm caressing his maid's cheek--his velvety lips pressing against Vito's, firm and sweet, lacking any of the harshness that lingered on those same lips only moments ago.

Vito was such a cute little thing in that getup, Henry would be lying if he said it didn't get him riled up. Not to mention, Vito was being rather sweet despite his sarcastic nature--but then again, submission will do that to a person. Make them something that they aren't, make them beg and plead, make them swallow their pride, make them forget their troubles. Vito did all those things.

Vito stopped at nothing to leave prints all over Henry's mouth and chin, and Henry did nothing to stop him. Soon enough, Vito's excitement grew to be too much to bear. With a soft groan, he put his own hand beneath his skirt to help himself--that is until Henry pushed it away.

"Nope, none of that, sweetheart…" he told Vito, "only I can touch you."

Vito let out a defeated whine as Henry replaced Vito's hand with his own. Vito's hands instead went to Henry's fly, eager to pull it down. 

Henry chuckled with amusement. 

"Like I said, " he began, "you're needy."

He gave the other a particularly hard jerk, granting him a sharp moan from his pathetic little servant. 

"Oh wow~.." Henry cooed, "you moan like a fucking whore…"

He took Vito's prying hand and pressed it to the inside of his thigh, where a bulge strained against the fabric of his slacks. 

"It kinda turns me on.."

Vito got the hint immediately and massaged what he so desired, all the while panting and whimpering at the effects of Henry's handiwork.

Vito's breath grew even more unsteady, his mouth open to say something while he gasped. He arched his back, whined as his toes curled within his chunky heels, moaned as he heard Henry praise him in his ear, telling Vito how good he was being, how his noises kept his master waiting for his turn. 

Vito trembled as his body was pushed over the edge, his tender shaft pulsing and jumping against the man’s warm grip. His pleasure revealed itself in the form of quick moans and whimpers, as well as the profanities that poured from his lips.

"Oh..oh, fuck! Fuck! Shit, oh shit..!" He hissed, letting his hips override any rational thoughts he had left, turning into a puddle of mush as he came down from his all-time high.

Henry smiled as he glanced at the mess Vito made on his hand. 

"Aww, are we all finished?" He teased, wiping his hand on Vito's pastel underwear. 

Vito couldn't look him in the eye, his embarrassment controlling him, humiliation biting his tongue.

"It's okay, sugar," the man assured, "after all, we both know that I ain't got mine yet…"

He gripped the bulge in his pants to drive the point home, an action that chucked the embarrassment out of Vito's body.

"and we all know that's what I really want."

Vito's hands shook as they lingered in the crisp air, Henry's belt buckle just, if not, colder than the surrounding temperature. The leather strip came undone rather easily, the silver button taking a few tugs to get it off. Vito ignored Henry's mocking snicker and continued his quest to quench his thirst. The sound of the zipper crawling down the metal teeth rang in his ears, his anticipation rising. Henry swore he heard Vito squeal with excitement from below as his hands traced over what had been brewing ever since the perverted idea was brought to his attention. His painted nails eagerly peeled the waistband of his master's boxers down, his prize springing forth from its confines, hanging a little from its own weight.

Vito's eyes fell shut as his lips pressed against the warm flesh, his nose inhaling the musky smell Henry's cologne had to offer, his palms resting on Henry's thighs. With an exhale from his nostrils, the kiss turned into a sensual swallow, his master's silence dissolving into a hushed groan. Vito tittered at his vocals, deciding to have a little more fun with it all, using his touch to pump up the heat between them, using his velvety tongue to caress what stood between him and Henry's six-second bliss. The world around them became nothing but cold air. Anyone who dared to knock on the office door was in for a scene, and both of them could care less. 

Vito was sucked into the rhythm of his action, his ears only paying attention to the sultry noises of gratitude that left his master's mouth. 

“I love your passion, hun…” he cooed, “remind me to pay you back after this."

The only response Henry received was a nonverbal one, Vito's blush was a good enough reply. 

Henry's reaction to Vito's effort was far from nonverbal.

"Damn..!” he cursed, “you’re good…” 

Vito hummed in appreciation as he pushed further, the tip of his nose coming close to Henry's undone zipper, nearly touching the tiny, metal, teeth.

“Yeah!” Henry growled, his nails digging into the servant’s scalp, “that’s it…”

He took delight in Vito's gags as he pushed his head lower, chuckling in sadistic glee as his thighs tingled with the scratches and scrapes of the maid's pretty, painted, claws. Vito's eyes squinted as he coughed and choked when the man took control of his pace, only able to breathe once Henry pried his grip off Vito's skull. 

“Hmm..too much?” he inquired.

Vito could only answer in gasps and coughs.

“No sir,” he replied, wiping his mouth clean and sniffling.

With that, Henry took matters into his own hands, gripping what Vito had to work with and pointing it at his lips. 

“Keep going, then…” Vito heard him say as he took the slippery object into his mouth again, tasting, feeling, and worshipping his treat. His mind drifted to a distant wonderland, his eyes fluttered shut. The smell of sweat and woodsy cologne pierced Vito's nostrils, intoxicating him, luring the young man into a biddable state of mind. 

“That’s it, sweetheart, just a little more~..” Henry cooed as he returned his strong hand to the back of Vito's head

Vito treated him with care, using Henry's pleasure as an ego booster of sorts as he ran his tongue over all the curves of his toy. He reveled at the feeling of his hair being tugged by the serious, suited man, giggled at the way his legs trembled when he licked a certain spot. 

However, with a push of Henry's hips and a strangled groan, Vito's hand quickly went back to gripping his thighs, his brows furrowing as he felt him clutch onto his head with both of his rosy appendages. A wet “hurg-ack!” sounded throughout the room with every shove Henry gave, a grunt accompanying every other gag.

“That’s it pretty boy, ” he hissed between gritted teeth, “Just like that!”

The front of his slacks became a slobbery mess as he held Vito there, pushing in and out slowly.

The slight tug of his hair reminded Vito of his position, of his devotion. Slurps turned to moans, moans turned to curses, a kind, tender, idol turned into a rough, impatient, villain.

“seems like you're gonna get your--your weekend bonus early..” panted Henry, using the meat of his palm to push Vito’s head back, forcing the slippery totem to fall from his messy lips. He tugged on the maid's hair again, harder this time, causing Vito to wince.

Before he could protest about why he was pushed away from his task, a drawn out, shaky groan stole his attention, 

"Fuck!” groaned Henry, hunching over as he painted Vito's face with warm, white streaks, grunting as he finished up. For a moment, time slowed as they came down from their high, finding themselves back on earth. 

Vito looked up at him, his circumstantial paycheck plastered all over his lips and nose, some of it dripping from the corner of his mouth. Henry smirked with a chuckle. 

"Sorry 'bout the mess, doll." He said smugly.

Vito wiped his mouth again and stayed on his knees. 

"Will that be all, sir?" Vito questioned.

With a tuck of his prick and the zip of his fly, Henry was as poised as ever. He hardly looked like he had gotten blown by his little boytoy.

"Well, the dishes still need cleaning." He confirmed, as he kneeled, wiping the other’s nose with his thumb.

Vito nodded as Henry stood back up, prompting Vito to do the same.

"Yes sir." Vito replied.

Henry smiled warmly before giving Vito another soft kiss. 

"But that can wait til next time." He told his lover, "The missus will be here any minute."


End file.
